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Kerrying On

Kerrying On: Confessions of a Professional Trick-or-Treater

One crisp October day as I walked home from school with Rick Eherenfield (my grade-school best friend), he asked me a rather naïve question: “Would you like to go trick-or-treating with me next week?” What a rube! Didn’t he know anything about the finer art of extracting candy from strangers? First of all, it’s a huge mistake to go door-to-door with friends. When you travel with friends, you slow down as you talk.

Trick-or-treat rule number one: Don’t slow down for anything. During the precious few hours of the one night of the year when candy is free for the asking, chatting with a friend could cost you a chocolate candy bar—which, by the way, just happens to be your only reason for going out in the first place. (It’s all about the chocolate.) One Halloween, I sprinted by a house that was on fire and didn’t break stride. You think I’m going to go trick-or-treating with a friend?

Here’s another time-related hint. Today’s kids typically tote plastic pumpkins and similar store-bought containers for holding their goodies. I carried, and I’m not making this up, a burlap bag that had once contained a hundred pounds of potatoes. I didn’t have time to be swapping out tiny totes in the middle of the evening—ergo, the massive potato sack. Of course, the bag came at a cost. By the end of the evening it weighed just as much as I did and looked positively gluttonous. “Look at that thing!” adults would shout as I held open a bag large enough to schlep a yak. “It’s disgusting!”

Rule number two: Run from door to door. When you only have a four-hour window to get free candy, you run between houses. You don’t walk, you don’t jog, and you don’t even trot. You run. You also need to take advantage of the entire evening. I was always the first and last kid on the street. Every year my Halloween adventure started with someone shouting: “It’s not time yet you moron! I’m still doing the lunch dishes!” and ended with: “You woke me out of a dead sleep!”

Rule number three: Put the trick back in trick-or-treat. The candy companies of the fifties didn’t produce the pathetic miniature bars they now make in such abundance, so when someone gave you a candy bar back in my day (and I firmly believe this qualified them for sainthood), you got a full-sized one. This didn’t happen very often, but when it did, you scored big.

So, here was the trick. I’d carry several masks. I didn’t normally don a mask because it would limit my vision and slow me down. But if someone gave me, say, a Hershey bar (most people gave out penny candy) I’d hit a couple of nearby doors, put on one of my masks, and return to the place that was giving out the mother lode. I would repeat this stunt with a different mask until I got caught. “Say, haven’t you been here before?” Using the mask trick, you could score as many as a half dozen full-sized candy bars at a single house.

Rule number four: Beware of baked goods. I was raised at a time when a handful of elderly homemakers still made pumpkin-shaped cupcakes frosted with an inch of gooey chocolate icing. They’d beam with pride when they opened their front door. “Here you go, sonny,” they’d say as they held out a tray full of their sticky creations while eyeing my burlap bag suspiciously. Now, what was I supposed to do with a gooey cupcake? Consuming it was out of the question. That violated the fifth rule of trick-or-treating: Never eat on the job.

One year, I made the grievous error of letting a well-intended grandmother drop a cupcake into the center of my burlap bag. I swear the chocolate-covered treat had its own gravitational field—sucking every decent piece of candy into its icing atmosphere until, by the end of the evening, it had grown to the size of a basketball. I learned to take cupcakes gingerly in my hand and then use them to mulch the neighbors’ flower beds.

Now for today’s broader (and less Halloween-y) lesson. Before chronicling my trick-or-treating habits for this column, I had never shared my Halloween techniques with my own children. As helpful as the information might have been for them, I kept my goofy methods a secret for fear of revealing that at one time I was greedy, weird, and (dare I say it) a bit of a nerd. I wanted my kids to think I was cool. Is that asking so much? This reluctance to share an unflattering side of our personality comes at a tremendous cost. When we eagerly share our accomplishments but not our embarrassing moments, weaknesses, and vulnerabilities, we’re less human. We’re hard to connect to. We’re not particularly interesting to hang out with.

This desire to keep up an impeccable image also plays a big role at work. I’m confident in assuming that almost everyone in corporate America has a file full of stories similar to my Halloween tale that they’d rather keep locked away rather than air them in front of their friends and coworkers. To ensure our rosy reputations and bolster our own self-esteem, we primarily share lists of accomplishments, notable experiences, and tales that make us out to be a hero.

Ironically, sharing a steady stream of accomplishments can create more fragmentation than unity. Perfection is tiring. It feeds jealousy. It’s hard to relate to. At a time when organizations expect employees to coalesce into high-performance teams, it becomes just that much more difficult for employees to bond with others when all that coworkers know about each other is what can be found on their hyperbolic, sanitized resumes.

Fortunately, it doesn’t have to be this way. Unity finds a foothold in any environment where individuals willingly share a more balanced picture of themselves than is currently the rage. By occasionally sharing fears, missteps, and trick-or-treating oddities we become unthreatening, relatable, and likable. We become someone who makes a good friend or teammate.

So, let’s strip away our masks this Halloween season and dare to be the normal (quirky) people that we are. Consider sharing a more complete image of yourself, not one that’s hidden behind masks of solemnity, perfection, and accomplishments; rather, share with friends, family, and coworkers glimpses of the more interesting you—the childlike you—the oddball you. For instance, did you dunk for apples as a teenager until you choked and spit up on your date? Did you make your own costume for a neighborhood competition only to have critical parts of it fall off during the awards ceremony? Or, as related earlier, did you aggressively knock doors on Halloween night until someone finally shouted: “Hey kid, it’s time for you to haul your potato sack home!”

Sharing stuff like that binds people together.

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10 thoughts on “Kerrying On: Confessions of a Professional Trick-or-Treater”

  1. Jeff Grigg

    Who am I to criticize your youthful Halloween habits? You knew what you wanted. You took direct effective actions to get it. You optimized the process to maximize the value you wished to produce. And, while you took it further than most, you’re not alone: I’ve had *plenty* of late teenage kids come to my door carrying pillow cases full of candy. I don’t criticize them. They’re “working the system” to get what they want.

    In our family, we’ve always emphasized the social experience over the competitive game of “scoring the most candy.” Costumes, decorating, giving, interacting with friends and neighbors were important to us. And we always ended up with more than enough candy to make us sick and fat anyway. And we didn’t really need Halloween to get and eat candy, if we really wanted it. If I get it myself, I can get the kinds I most like.


    We all have our funny stories to tell about our history.

    I like to think that one of my “defining moments” was when I jogged over to the neighbors house, found him in his garage, and I said, literally, “Did you know that your back yard is on fire?” He said, “You’re kidding.” And I said, “No.” I was not kidding. I’m kind of literal minded that way. It occurred to me to ask if he knew if his back yard was on fire because I found him puttering with a boat motor in his garage — as one might do if one was unaware of the explosion and fire under pine trees in the back that could easily destroy both of our houses. He ran to his back yard to pick up his garden hose and fight the fire.

    Our family did tend to be “calm under fire” like that: What happened a minute or two before then was that we were eating dinner in our dining room and we heard a “pop” of a small explosion outside, and saw several small “fire balls” drop into our back yard. My father got up and told my mother to use the hose in the front yard, my sister to call 911, me to go tell the neighbor, while he went into the back yard to fight the fire with the garden hose there. And that’s what we did. By the time the fire department arrived, from a block away, the fire was out.

  2. Jenna

    This was not only a very entertaining read, but the end part about embracing your quirkiness really resonated with me. Thank you and Happy Halloween! (your kids should be sad you didn’t share your trick or treat tips with them.)

  3. Alan A Janak

    Great story, reminds me of our using pillowcases for candy (really!), but when they dragged on the ground and made holes in them, so the candy leaked out, it kind of defeated the purpose! Thanks for the memories!

  4. Ali Kinney

    Thank you, Great story and poignant tie-in with today’s workplace atomosphere.

  5. Alane Howerton

    Loved it Kerry! I remember going for it on Halloween! What’s up these days kids just don’t want to hustle for candy! :))

  6. Todd Taylor

    Thank you! Refreshing! Much appreciated!

  7. Amy Green

    That is funny!! And good lesson at the end too; reminds me of JP Sears’ TED Talk on saying yes your weirdness. It’s both hilarious and profound.

    My 10yo is the opposite of this; she doesn’t have a sweet tooth and what she loves is dressing up in costume, then slowly mozying, looking at the decorations and chatting with the people handing out candy. Therefore, she can never trick-or-treat with friends because they leave her in the dust!

  8. Chris

    Dear Patterson, I enjoyed your confession and wisdom of being less impeccable. I also learned something new that we may become less threatening, and perhaps more relatable we are less a treat

  9. Helene

    Great story!! As a short adult I’ve thought about trick or treating in recent years!

  10. Advanced Reading Concepts

    I loved this. Fun, timely and thought provoking.

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